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Biomimetic oxidation studies. 7. Alkane functionalization with a MMO structural model, [Fe2O(OAc)(tris((1-methylimidazol-2-yl) methyl) amine)2]3+, in the presence oft-butyl hydroperoxide and oxygen gas

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Abstract

A biomimetic structural model of the active site of methane monooxygenase enzyme, [Fe2O(OAc)(tris((1-methylimidazol)-2-methyl)amine2]3+, 1, has been shown to functionalize cyclohexane, toluene, adamantane, propane, and ethane in the presence oft-butyl hydroperoxide and oxygen gas. A mechanism is proposed to account for these results which implicates an alkyl hydroperoxide intermediate to the alcohol, ketone, and aldehyde products in an oxygen gas dependent reaction, while aldehyde and ketone products can also be formed from the further oxidation of the alcohols in an oxygen gas independent reaction.

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Authors and Affiliations

  1. Lawrence Berkeley Laboratory, University of California, 94720, Berkeley, CA, USA

    Richard H. Fish & Kenneth J. Oberhausen

  2. Department of Chemistry, University of Louisville, 40292, Louisville, KY, USA

    Shan Chen, John F. Richardson & Robert M. Buchanan

  3. Department of Pharmacology, University of Louisville, 40292, Louisville, KY, USA

    William Pierce

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  1. Richard H. Fish
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  2. Kenneth J. Oberhausen
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  3. Shan Chen
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  4. John F. Richardson
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  5. William Pierce
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  6. Robert M. Buchanan
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Fish, R.H., Oberhausen, K.J., Chen, S. et al. Biomimetic oxidation studies. 7. Alkane functionalization with a MMO structural model, [Fe2O(OAc)(tris((1-methylimidazol-2-yl) methyl) amine)2]3+, in the presence oft-butyl hydroperoxide and oxygen gas. Catal Lett 18, 357–365 (1993). https://doi.org/10.1007/BF00765282

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  • DOI: https://doi.org/10.1007/BF00765282

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